Representing the NAACP, he successfully challenged school segregation in the landmark Supreme Court case, Brown v. Board of Education (1954).

Due to residential segregation and changes in the demographics of Baltimore, as of 2008[update] the overwhelming majority of students at Douglass were African American and many were poor.

On June 22, 1894, a year before his death, Frederick Douglass gave a commencement address at what would become a namesake school, saying: "The colored people of this country have, I think, made a great mistake, of late, in saying so much of race and color as a basis of their claims to justice, and as the chief motive of their efforts and action.

By 1938, Coppin had developed a four-year curriculum and the college began to grant Bachelor of Science degrees.

[9] The high school moved in 1925 to its third location, a new building specifically designed for the high school was constructed of red brick and limestone trim, in the English Tudor / Jacobethan style, on the intersection at Calhoun and Baker Streets, but without a surrounding campus but facing directly on surrounding sidewalks.

Since 1954, following the racial integration of Baltimore City public schools, Douglass High has been located on Gwynns Fall Parkway across from "Mondawmin" - the noted city financiers' Alexander and George Brown's estate, one of the last rural country estates in the city, which was shortly after razed and redeveloped as Mondawmin Mall by developer James Rouse (also did "Harborplace" in Inner Harbor in 1979–1980) in the previous Western High School building and extensive landscaped campus, constructed in 1927–1928.

They shot the film during the 2004 - 2005 school year, highlighting its history and its academic and financial struggles while working to comply with the No Child Left Behind Act.